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Molecular packing and the handedness of the self-assemblies of C17H35CO-Ala-Phe sodium salts

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Abstract

The handedness of the self-assemblies of several series of homogeneous lipodipeptide sodium salts is controlled by the chirality of the amino acid at the C-terminus. This phenomenon is named the “C-terminal determination” rule. Herein, four heterogeneous C17H35CO-Ala-Phe sodium salts, designed and synthesized by changing the chirality of the amino acids, were able to self-assemble into twisted nanoribbons in deionized water. The handedness of the nanoribbons was controlled by the chirality of the alanine, which does not follow the “C-terminal determination” rule. This phenomenon might be because the homochiral and heterochiral lipodipeptide sodium salt molecules packed into different structures. The X-ray diffraction and circular dichroism characterizations indicated that the molecules self-assembled into an interdigitated bilayer structure and there were no strong π–π stackings between neighboring phenyl groups.

Graphical abstract: Molecular packing and the handedness of the self-assemblies of C17H35CO-Ala-Phe sodium salts

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Publication details

The article was received on 14 Jul 2017, accepted on 25 Sep 2017 and first published on 26 Sep 2017


Article type: Paper
DOI: 10.1039/C7NJ02553J
Citation: New J. Chem., 2017, Advance Article
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    Molecular packing and the handedness of the self-assemblies of C17H35CO-Ala-Phe sodium salts

    S. Lin, Y. Li, B. Li and Y. Yang, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ02553J

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